I know this topic is a frequent one...but someone please offer me some real world advice. I know the "rules" so please no need to tell them to me here, but I want to know what to actually do based on what probably/might/could actually happen.

I am an American, entered Italy almost 90 days ago as tourist. Tourist visa about to expire. IMPORTANT FACT: when I entered Italy almost three months agao, my passport was NOT STAMPED. They just looked at it. In fact, the only stamp I have on my passport was from when I entered Italy LAST YEAR, (so from Italy's perspective, it might even seem like i have been here for over a year!)

I am going to outstay the visa. Risky I know. Here is the question. I will most likely return to the US in April, two months after the expiration date. I am then going to try to REENTER Italy TWO WEEKS LATER in April.

Questions:
1. How realistic is it that I will get caught at any point in the process above? Meaning, if I pass through customs on my way out without any question, will that mean I will have no issue getting back in two weeks later? Or if I pass through on the way out, could I still get caught on my way in again when I try to reenter in April? If so, would they literally return me home on the next flight to the US?
2. How relevant is the fact that I dont have a stamp on my passport from when I entered Italy two months ago? SHOULD I leave Italy and come back within the 90 days (two weeks left) so I CAN get a stamp so it appears as if I JUST entered Italy "for the first time" now to avoid the 90 day dilemma because my Passport will "look like" I have just arrived here?
3. Any tricks on how to overcome any of this? I am a cute unassuming girl, does that help my situation? Maybe I can slide through customs that way??? I know sounds silly, but I am talking reality here...that is what actually happens, not theory of laws....THANK YOU!!! PLEASE HELP!!